Craziest Men's Style and Fashion Trends in the Last 20 Years - Mandatory
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Craziest Men's Style and Fashion Trends in the Last 20 Years

Related: fashion fails, Mens Fashion, Style and Grooming

By Gary Dudak Oct 16, 2012

  • glamourmagazine.co.uk
    1 of 38

    Generally, men care a lot less about style and fashion than women. Yet, over the past 20 years, we still managed to create some pretty terrible styles that were followed by our fellow men and encouraged to the point of becoming acceptable trends. Here are some of the most ridiculous mens style and fashion trends we have seen since the early 1990s.

    Trucker Hats

    Ashton Kutcher will be seen a couple times on this list, but it was his popularizing of the trucker hat in the early 2000s that was his most egregious fashion fault.

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  • geeksugar.com
    2 of 38

    Cell Phone Belt Clips

    Typically can be seen on the belt of the same guy rocking a bluetooth earpiece.

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  • Steve Granitz/WireImage.com
    3 of 38

    Guyliner

    Synonymous with emo, metrosexuality and Peter Parker in "Spider-Man 3," eyeliner for guys is a style trend that should never come back.

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  • popdust.com
    4 of 38

    Frosted Tips

    Men bleaching all of their hair was also an inexplicable style craze once, but frosted tips may have been worse.

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  • Francois Durand/Getty Images
    5 of 38

    Faux Hawks

    Musician and actor Jared Leto actually provides us with three ridiculous style examples here: the faux hawk, the aforementioned bleached hair, and obnoxious sunglasses.

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  • Thinkstock
    6 of 38

    Wallet Chains

    Let's be honest. Most men who wore wallet chains didn't have the bankroll to warrant the wallet security anyway.

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  • countryuniverse.net
    7 of 38

    Shell Necklaces

    We'll ignore the country hat since Kenny Chesney is a country music star, but there's really no excuse for him rocking the tight puka shell necklace.

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  • mulletjunky.com
    8 of 38

    Mullets

    The mullet-mania of the 1990s resulted in a lot of laughs and maybe peaked with the 2001 movie "Joe Dirt," but no self-respecting man should ever consider sporting one (unless they lost a bet and have to pay up).

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  • 9 of 38

    Jean Shorts

    Also known as jorts, no fashion trend will make you look more like a dorky dad than jean shorts...except for maybe the fanny pack.

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  • 10 of 38

    Fanny Packs

    If you would like to be able to carry all of your valuables in one convenient bag, get a girlfriend and take advantage of her purse.

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  • Chey Rawhoof/Flickr
    11 of 38

    Ear Gauges

    Have you ever looked at your earlobe and thought, "Man, I really wish I could stick my finger through there?" For alternative rockers everywhere, the answer was yes.

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  • thedetailedimage.com
    12 of 38

    Manpris

    Not quite shorts, not quite pants, not quite cool.

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  • ebaumsworld.com
    13 of 38

    Bling Bling

    Worn by hip hop artists, drug dealers and athletes who just signed multimillion dollar contracts. The more bling you wear, the higher your perceived social status, and the more likely you are to one day file for bankruptcy.

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  • refinery29.com
    14 of 38

    Seinfeld Style

    Colorful button-up shirts sometimes tucked into mom jeans and complemented with sneakers was a look that never hindered Jerry's ability to pick up women, but it's one that should never be imitated again.

    Related: Seinfeld's Most Ridiculous Outfits

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  • Thinkstock
    15 of 38

    Mandals

    If you're going to cover up that much of your foot, just wear shoes.

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  • laist.com
    16 of 38

    Zubaz

    This outrageous brand of pants was popular in the early 1990s and can still be found in the drawers of overweight football fans to this day.

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  • Andy Lyons/Getty Images
    17 of 38

    Sweat Suits

    Worn by basketball coach Bob Huggins and wannabe mafia types. Full-body comfort will not disguise the fact that a slob is underneath.

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  • Jeffrey Ufberg/WireImage.com
    18 of 38

    Socks With Sandals

    Before he became Snoop Lion, he was just Snoop Lazy.

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  • dickies.com
    19 of 38

    Carpenter Jeans

    Should only be worn by real carpenters. No exceptions.

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  • menshair.about.com
    20 of 38

    Chinstrap Beards

    It takes way too much time and effort to groom your beard into a nice thin line around your face, especially when said thin line beard makes you look like an A-hole.

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  • mensfashion.about.com
    21 of 38

    Deep V-Necks

    If you are constantly complaining about having an abnormally warm chest and need to get it some air, a deep V is OK. Otherwise, do not wear them.

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  • zimbio.com
    22 of 38

    Ed Hardy/Affliction Attire

    Any style related to the men of "Jersey Shore" should be avoided like the plague.

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  • 23 of 38

    Flat Bill Hats with the Sticker On

    This is one of those fashion trends that had to have started by accident. Perhaps it went down like this:

    Guy 1: Hey man, cool new hat, but you forgot to take the sticker off.

    Guy 2 (embarrassed): Uhh, no! I meant to leave it on. It's a cool new style that everyone's doing.

    Guy 1 (stupid): Sweet!

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  • George Pimentel/Getty Images
    24 of 38

    The Soul Patch

    "America's Got Talent" judge and apparent comedian Howie Mandel is practically hairless, except for the creepy triangle of facial hair he keeps below his bottom lip. It's commonly viewed as a sad attempt to be youthful and edgy...which also explains the double hoop earrings.

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  • complex.com
    25 of 38

    Layered Polos

    Along with popping collars, this fashion trend blew up sometime around 2002-2003, and frat houses have never been the same (just kidding, they are still exactly the same).

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  • 26 of 38

    Bowl (Mushroom) Haircut

    In the early 90s, not only did many young men and boys have mushroom haircuts, they were proud of it. You weren't cool unless your mom put a bowl around your head and trimmed the hair underneath. Makes sense.

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  • styleforum.com
    27 of 38

    JNCO Jeans

    These insanely wide boys and mens jeans gained recognition in the 90s, and gobbled up the shoes of many skaters, ravers and Juggalos in the process. They looked like someone took two large jean skirts, sewed them together, added some large pockets and sewed crazy emblems on at the end.

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  • myflyculture.com
    28 of 38

    Nameplate Belts

    It doesn't matter what word you were displaying on your belt, the message was the same: JACKASS.

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  • 29 of 38

    Parachute Pants

    MC Hammer's super hit single "U Can't Touch This" came out in 1990, yet the silly pants he wore and made popular were widely accepted as an OK style for many years to come. What were we all thinking?

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  • fashionindie.com
    30 of 38

    Sagging

    When your underpants are no longer under your pants, you just look like a damn fool.

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  • allhiphop.com
    31 of 38

    Tall Tees

    XXL t-shirts for guys who belong in the medium section. There is no explanation for wanting to wear a shirt that is more like a dress, but if your saggy jeans fall off it may come in handy.

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  • fashionbombdaily.com
    32 of 38

    Pointy Shoes

    Widely regarded by hot women like Hope Dworaczyk as the most hated mens fashion trend, pointy toe shoes will make you look as desirable as the Keebler Elf.

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  • YouTube/kirkzipfel
    33 of 38

    Skinny Jeans

    "They're kinda 'in' right now" is something that losers say. If you own them, they should remain 'in' your closet.

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  • 34 of 38

    Tight-Rolled Jeans

    A carryover from the ridiculous style of the 1980s, tight-rolling your jeans was a good way to fit in with the cool crowd in the early 90s - and also keep your socks from falling down.

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  • my350z.com
    35 of 38

    Visors

    How an article of clothing that should only be worn on the golf course made its way to the mainstream and got turned backwards and flipped upside down is beyond me, but Jamie Kennedy sure is grateful.

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  • 36 of 38

    Wind Pants

    The ironic part about wind pants is that they are most useless when you are out in a lot of wind. Yet, walking around in garbage bag material pants was once widely accepted and deemed appropriate. Consumers are idiots.

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  • dcclubbing.com
    37 of 38

    Grills

    Also spelled Grillz (if you're cool). Most people try to avoid dental work, but in the hip hop culture in the mid-2000s, Dirty South rap started to rise and mouth jewelry became highly sought after. They may cost a lot and lead to further dental health problems, but if Paul Wall and Lil Jon are doing it we all better jump on board!

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  • 38 of 38
    Next: Epically Hilarious Photos

    Crocs

    The picture pretty much says it all.

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debra salama

I live in Cairo Egypt and those pointy shoes are Huge here Belieive it or not, the metrosexual thing is hot here too. Guys wearing hot pink and lavendar together, supertight shirts and pants, looking like they raided their sisters closet. In the States they would be laughed at then buttfucked.

October 18 2012 at 4:38 AM Report abuse Permalink rate up rate down Reply
hello sexy mama

ok Jared Leto look like an moron, but anyways get on here but some of the stuff they said was bad fashion is mostly rock, metal type of style, the ear plugs, ya a bunch of rockers, punks, and metal heads sport that, which i think is hot on guys as long as its not over board with the plugs, the chain wallet only ppl that i know that where those are again punk, rockers, and bikers, the chinstrap beard just shows how much a douche you are, men the ed hardy stuff please stop no man should wear that much bing on a shirt unless you are gay, yes the mushroom bowl hair cut, u look like a penis with that haircut, who wears jncos anyways havent seen a pair since 1997,

October 17 2012 at 12:22 PM Report abuse Permalink rate up rate down Reply
gonensixty

The Big O.... Does not know she was sleeping with 1 of his previous guards in the past 2 yrs. I'm sure he is oblivious.., OMG he thinks he's Our god..,. She wears the pants.. LOL

October 16 2012 at 9:59 PM Report abuse Permalink rate up rate down Reply
sylvabugg2

With the state that his country is currently in you'd think they'd be more concerned about more important things, not what he's wearing.

October 16 2012 at 7:25 PM Report abuse Permalink +1 rate up rate down Reply
whell

Perhaps we could add some tired editorial trends such as the use of the word "rocking," as in "rocking a bluetooth earpiece," or "rocking the tight puka shell necklace."

October 16 2012 at 7:19 PM Report abuse Permalink rate up rate down Reply
jazzdeux

Don't usually read these silly pieces but read this one on men's craziest fashions. Agreed with all but one. Sometimes a cell phone clip is necessary even if one doesn't like it (and I don't). But then I clicked to read the author's bio to see who was behind this weird but interesting little piece of fashion judgment and saw the author's baseball hat on backwards--a piece of fashion that is as bad as many of the fashion statements he mocks. A backward baseball hat--come on. You talk about a bad fashion statement. Just sayin' . . .

October 16 2012 at 7:18 PM Report abuse Permalink +3 rate up rate down Reply
1 reply to jazzdeux's comment
dugar12

Yeah, but still pretty hunky right?

October 16 2012 at 8:21 PM Report abuse Permalink +2 rate up rate down Reply
Dragonwolf

Ok I actually waisted my time reading the captions here, and one thing struck me like a mack truck doing 90 hitting a wall. That is how superficial, judgemental, and arrogant some people are. I mean seriously to judge others based on what they wear or a haircut? To all the "fashion police & faasionista's" out there I say this GET A ******* LIFE!

October 16 2012 at 5:31 PM Report abuse Permalink +1 rate up rate down Reply
1 reply to Dragonwolf's comment
howardstern111

to all the ******** writing hate mail on a fun and funny story "get a life" this piece was hilarious and supposed to be lighthearted. way to bring it down.

October 16 2012 at 8:51 PM Report abuse Permalink -1 rate up rate down Reply
missltm1

Those are not Parachute pants, they are Hammer pants.

October 16 2012 at 5:26 PM Report abuse Permalink -1 rate up rate down Reply
jetdogy

How nerdy!

October 16 2012 at 4:52 PM Report abuse Permalink -1 rate up rate down Reply
jetdogy

So gay!

October 16 2012 at 4:51 PM Report abuse Permalink rate up rate down Reply
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